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Chemical Compound Review

Oxalamic acid     aminocarbonylmethanoic acid

Synonyms: oxamate, Oxamidic acid, CHEMBL15976, OTAMIC ACID, OXAMIC ACID, ...
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Disease relevance of oxamic acid

  • A number of oxamic acid derivatives of tropones and tropolones were synthesized and their antianaphylactic activity was determined in passive paw anaphylaxis (PPA) [1].
  • The mechanism of activation of the lactate dehydrogenase from Streptococcus faecalis by fructose 1,6-bisphosphate was investigated by using the immobilized oxamate gel [2].
  • Trypanocidal activity of N-isopropyl oxamate on cultured epimastigotes and murine trypanosomiasis using different Trypanosoma cruzi strains [3].
  • Convenient routes to methyl 2-oxalylimino- and 2-(phosphonoformimido)-3,3,3-trifluoropropanoates have been elaborated, based on the reaction of methyl trifluoropyruvate with ethyl oxamate or diethyl carbamoylphosphonate, respectively, followed by dehydration [4].

High impact information on oxamic acid

  • We have determined by X-ray crystallography the structures of PFL (non-radical form), its complex with the substrate analog oxamate, and the C418A,C419A double mutant [5].
  • Rate-limiting steps for hepatic gluconeogenesis. Mechanism of oxamate inhibition of mitochondrial pyruvate metabolism [6].
  • We examine here the dynamics of forming the Michaelis complex of the enzyme lactate dehydrogenase by characterizing the binding kinetics and thermodynamics of oxamate (a substrate mimic) to the binary lactate dehydrogenase/NADH complex over multiple timescales, from nanoseconds to tens of milliseconds [7].
  • The dynamics of the mobile loop, which closes over the active site and is important for catalysis and binding, were characterized by studies of the inhibitor oxamate binding to the LDH/NADH binary complex monitoring the changes in emission of bound NADH [8].
  • Synthesis and structure-activity relationships of oxamic acid and acetic acid derivatives related to L-thyronine [9].

Biological context of oxamic acid


Anatomical context of oxamic acid

  • The thermodynamics of the reaction catalyzed by pig heart muscle lactate dehydrogenase (LDH; EC1.1.1,27) have been studied in 0,2 M potassium phosphate buffer, pH 7, over the temperature range of 10 to 35 degrees C by using oxamate and oxalate to simulate the corresponding reactions of the substrates pyruvate and lactate, respectively [15].
  • In the presence of oxamate, fatty acid oxidation inhibited gluconeogenesis from lactate, alanine, and low pyruvate concentrations (less than 0.5 mM), and the rate of transfer of reducing equivalents to the cytosol was significantly decreased [16].
  • The decreased pyruvate carboxylase flux does not seem to be the result of a direct inhibitory action of oxamate on this enzyme but is secondary to a decreased rate of pyruvate entry into the mitochondria [16].
  • Oxamate also gave greater than additive cell killing in multicellular spheroids when combined with Dox and there was a greater than additive growth delay in spheroids dosed with Dox plus oxamate [14].
  • LDH-C4 activity was 5.52 +/- 3.41, 15.72 +/- 6.04 and 15.22 +/- 1.92 Units 1010 spermatozoa-1 in plasma membrane, sperm suspension and cytosol fraction, respectively; these activities were inhibited by sodium oxamate [17].

Associations of oxamic acid with other chemical compounds

  • This interpretation appears very probable in view of recent x-ray crystallographic studies on lactate dehydrogenase from dogfish, which demonstrate a volume decrease to occur on binding of oxamate to the LDH-NADH complex [15].
  • In addition, inhibition of the HCO3(-)-dependent MgATP cleavage by both avidin and oxamate indicate that although biotin does not directly participate in the reaction, its presence is required in that part of the active site of the enzyme [18].
  • The oxamate group in the title compound, C(10)H(11)NO(3), is almost coplanar with the phenyl ring because of intramolecular hydrogen-bonding interactions, and the structure can be described as an anilide single bonded to an ethyl carboxylate group [19].
  • Western blotting showed that oxamate and N-isopropyl oxamate inhibited the tyrosine phosphorylation of proteins during the sperm capacitation process [20].
  • Arsenite but not oxamate produce in vitro a distinct depression of estrogen-dominated uterine motility, both in the absence of substrate as well as in the presence of exogenous glucose or lactate [21].

Gene context of oxamic acid

  • The complex pH profile for inhibition of CA I by the ambivalent oxamate is consistent with coordination through the carboxylate group at low pH and through the deprotonated amide group at high pH [10].
  • However, the affinity of oxamate for the enzyme--NADH complex was decreased by 100-fold and it was calculated that this constituted a net increase of 10.4 kJ/mol in the activation energy for binding [22].
  • The competitive nature of oxamate inhibition is in conflict with its effect on isolated pyruvate carboxylase which is noncompetitive for pyruvate [16].
  • RESULTS: Under normal oxygen tension, we find that the pancreatic cell line MIA PaCa2 (1420) is 7 times more sensitive to 2-DG and equally sensitive to oxamate, as compared with Panc-1 (1469) [23].

Analytical, diagnostic and therapeutic context of oxamic acid


  1. Troponoids. 3. Synthesis and antiallergy activity of N-troponyloxamic acid esters. Bagli, J.F., Bogri, T., Palameta, B., Martel, R., Robinson, W., Pugsley, T., Lippmann, W. J. Med. Chem. (1979) [Pubmed]
  2. Affinity chromatography of bacterial lactate dehydrogenases. Kelly, N., Delaney, M., O'Carra, P. Biochem. J. (1978) [Pubmed]
  3. Trypanocidal activity of N-isopropyl oxamate on cultured epimastigotes and murine trypanosomiasis using different Trypanosoma cruzi strains. Chena, M.A., Elizondo, S., Rodríguez-Páez, L., Nogueda, B., Baeza, I., Wong, C. Journal of enzyme inhibition and medicinal chemistry. (2005) [Pubmed]
  4. Methyltrifluoropyruvate imines possessing N-oxalyl and N-phosphonoformyl groups-precursors to a variety of alpha-CF(3)-alpha-amino acid derivatives. Skarpos, H., Vorob'eva, D.V., Osipov, S.N., Odinets, I.L., Breuer, E., Röschenthaler, G.V. Org. Biomol. Chem. (2006) [Pubmed]
  5. Structure and mechanism of the glycyl radical enzyme pyruvate formate-lyase. Becker, A., Fritz-Wolf, K., Kabsch, W., Knappe, J., Schultz, S., Volker Wagner, A.F. Nat. Struct. Biol. (1999) [Pubmed]
  6. Rate-limiting steps for hepatic gluconeogenesis. Mechanism of oxamate inhibition of mitochondrial pyruvate metabolism. Martin-Requero, A., Ayuso, M.S., Parrilla, R. J. Biol. Chem. (1986) [Pubmed]
  7. The approach to the Michaelis complex in lactate dehydrogenase: the substrate binding pathway. McClendon, S., Zhadin, N., Callender, R. Biophys. J. (2005) [Pubmed]
  8. Toward an understanding of the role of dynamics on enzymatic catalysis in lactate dehydrogenase. Gulotta, M., Deng, H., Deng, H., Dyer, R.B., Callender, R.H. Biochemistry (2002) [Pubmed]
  9. Synthesis and structure-activity relationships of oxamic acid and acetic acid derivatives related to L-thyronine. Yokoyama, N., Walker, G.N., Main, A.J., Stanton, J.L., Morrissey, M.M., Boehm, C., Engle, A., Neubert, A.D., Wasvary, J.M., Stephan, Z.F. J. Med. Chem. (1995) [Pubmed]
  10. Interaction of amide inhibitors with the active site of carbonic anhydrase: metal-induced deprotonation of the bound amide group is indicated by slow binding kinetics, by visible spectra of complexes with cobalt enzyme, and by pH effects on binding affinity. Rogers, J.I., Mukherjee, J., Khalifah, R.G. Biochemistry (1987) [Pubmed]
  11. (2-Carboxy-1,4-dihydro-4-oxoquinolyl)oxamic acids and (2-carboxy-1,4-dihydro-4-oxobenzo[h]quinolyl)oxamic acids as antiallergy agents. Wright, J.B., Johnson, H.G. J. Med. Chem. (1977) [Pubmed]
  12. Binding of oxalate to mitochondrial inner membranes of rat and human kidney. Laxmanan, S., Selvam, R., Mahle, C.J., Menon, M. J. Urol. (1986) [Pubmed]
  13. Expression of autocrine motility factor/phosphohexose isomerase in Cos7 cells. Lagana, A., Duchaine, T., Raz, A., DesGroseillers, L., Nabi, I.R. Biochem. Biophys. Res. Commun. (2000) [Pubmed]
  14. Modification of tumour glucose metabolism for therapeutic benefit. Hamilton, E., Fennell, M., Stafford, D.M. Acta oncologica (Stockholm, Sweden) (1995) [Pubmed]
  15. Thermodynamic studies of binary and ternary complexes of pig heart lactate dehydrogenase. Schmid, F., Hinz, H.J., Jaenicke, R. Biochemistry (1976) [Pubmed]
  16. Interaction of oxamate with the gluconeogenic pathway in rat liver. Martin-Requero, A., Ayuso, M.S., Parrilla, R. Arch. Biochem. Biophys. (1986) [Pubmed]
  17. Lactate dehydrogenase-C4 is involved in heparin- and NADH-dependent bovine sperm capacitation. O'Flaherty, C.M., Beorlegui, N.B., Beconi, M.T. Andrologia (2002) [Pubmed]
  18. Bicarbonate-dependent ATP cleavage catalysed by pyruvate carboxylase in the absence of pyruvate. Attwood, P.V., Graneri, B.D. Biochem. J. (1992) [Pubmed]
  19. Ethyl N-phenyloxamate. García-Báez E, E.V., Gómez-Castro, C.Z., Höpfl, H., Martínez-Martínez, F.J., Padilla-Martínez, I.I. Acta crystallographica. Section C, Crystal structure communications. (2003) [Pubmed]
  20. Inhibition of lactate dehydrogenase C4 (LDH-C4) blocks capacitation of mouse sperm in vitro. Duan, C., Goldberg, E. Cytogenet. Genome Res. (2003) [Pubmed]
  21. Effects of aresenite and oxamate on the in vitro functional activity of estrogen-dominated rate uterine horns. Gimeno, A.L., Goldraij, A., Gimeno, M.F. Experientia (1979) [Pubmed]
  22. A detailed investigation of the properties of lactate dehydrogenase in which the 'Essential' cysteine-165 is modified by thioalkylation. Bloxham, D.P., Sharma, R.P., Wilton, D.C. Biochem. J. (1979) [Pubmed]
  23. Differential sensitivity to 2-deoxy-D-glucose between two pancreatic cell lines correlates with GLUT-1 expression. Maher, J.C., Savaraj, N., Priebe, W., Liu, H., Lampidis, T.J. Pancreas (2005) [Pubmed]
  24. Structure of a ternary complex of an allosteric lactate dehydrogenase from Bacillus stearothermophilus at 2.5 A resolution. Wigley, D.B., Gamblin, S.J., Turkenburg, J.P., Dodson, E.J., Piontek, K., Muirhead, H., Holbrook, J.J. J. Mol. Biol. (1992) [Pubmed]
  25. Properties of human testis-specific lactate dehydrogenase expressed from Escherichia coli. LeVan, K.M., Goldberg, E. Biochem. J. (1991) [Pubmed]
  26. [3H]chloramphenicol metabolism in human volunteer: oxamic acid as a new major metabolite. Corpet, D.E., Bories, G.F. Drug Metab. Dispos. (1987) [Pubmed]
  27. Action of tioxamast on various models of anaphylactic shock, hyperreactivity and bronchial inflammation in guinea-pigs. Tarayre, J.P., Aliaga, M., Barbara, M., Tisseyre, N., Tisné-Versailles, J., Couzinier, J.P. Archives internationales de pharmacodynamie et de thérapie. (1991) [Pubmed]
  28. 96-well plate assay for sublethal metabolic activity. Yang, Y., Balcarcel, R.R. Assay and drug development technologies. (2004) [Pubmed]
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